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Despite receiving one of the biggest bailouts in history, AIG is considering whether or not to join its former chief executive, Hank Greenberg, in a lawsuit against the government for allegedly cheating its shareholders out of millions of dollars and violating the Fifth Amendment.

The wild thing about it, though, is that it was under Greenberg's tenure that AIG started investing in the financial instruments that almost brought it down in the first place.

To understand that, you have to understand that his history with the insurance giant goes back decades. In 1960, after serving in World War II and the Korean War, Greenberg joined C.V. Starr & Co. Inc. (a diversified financial services named after AIG's founder, Cornelius Vander Starr) as vice president. He currently holds the title of chairman and CEO of the firm.

Greenberg took over as president and CEO of AIG in 1967.

However, AIG and Greenberg have had a tumultuous relationship since Greenberg stepped down as CEO in 2005. He was forced out when an investigation by former New York attorney general Eliot Spitzer alleged that he "used off-balance sheet transactions to improperly boost profits."

The financial crisis in 2008 worsened his image within the company and in the public eye, despite overseeing 38 years of steady profit growth. Under Greenberg's tenure, AIG created the financial products unit that oversaw its credit default swaps (CDS).

These CDS were what brought AIG near bankruptcy when mortgage bonds that the company insured went under during the housing crisis. That left AIG stuck footing the bill.

Some argue that because Greenberg led the company when initial programs that engaged in credit default swaps were created, he indirectly precipitated the crisis.

"Hank Greenberg wandered out of the very safe, well-capitalized world of insurance into the surreal world of credit default swaps where you can create endless amount of risk," Christopher Whalen, co-founder of Institutional Risk Analytics, told Reuters.

Now he's suing the U.S. government for bailing AIG out after it almost collapsed under the weight of that risk. Wild.